Progress in Stereoselective Construction of C-C Bonds Enabled by Aldolases and Hydroxynitrile Lyases.

Mi Liu,Dan Wei,Zexing Wen,Jian-bo Wang

doi:10.3389/fbioe.2021.653682

Mi Liu, Dan Wei + Show 2 more

Open Access

https://doi.org/10.3389/fbioe.2021.653682

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Abstract

The creation of C–C bonds is an effective strategy for constructing complex compounds from simple synthetic blocks. Although many methods have been developed for C–C bond construction, the stereoselective creation of new C–C bonds remains a challenge. The selectivities (enantioselectivity, regioselectivity, and chemoselectivity) of biocatalysts are higher than those of chemical catalysts, therefore biocatalysts are excellent candidates for use in stereoselective C–C bond formation. Here, we summarize progress made in the past 10 years in stereoselective C–C bond formation enabled by two classic types of enzyme, aldolases and hydroxynitrile lyases. The information in this review will enable the development of new routes to the stereoselective construction of C–C bonds.

Highlights

Stereoselective construction of C–C bonds enables the formation of complex, enantiomerically pure, multifunctional macromolecular compounds from simple synthetic blocks
We summarize research progress in C–C bond formation enabled by aldolases and hydroxynitrile lyases (HNLs) in the last 10 years and focus on their stereoselective synthetic applications
In tests with benzaldehyde as the substrate, the ee value increased to 93% from the wild-type value of 55% (Asano and Kawahara, 2016)

Summary

INTRODUCTION

Stereoselective construction of C–C bonds enables the formation of complex, enantiomerically pure, multifunctional macromolecular compounds from simple synthetic blocks This provides an effective pathway for the production of important compounds such as natural products, pesticides, and pharmaceutical intermediates. Chemists have developed many excellent methods for constructing C–C bonds, such as Heck coupling (Andrus et al, 2002), Suzuki coupling (Suzuki, 2004), and Stille coupling (Jin and Lee, 2010). These methods can achieve high conversions and selectivities, but they involve toxic organic halogenations, require harsh reaction conditions, and have low atom economies.

H Lys-Enz OH N

Findings

CONCLUSION